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18.07.2008

Researchers from Rey Juan Carlos University and the University of Alcalá are developing analytical methodologies to quickly and efficiently evaluate asymmetric epoxidation processes of allyl alcohols.

Several industries, from pharmaceutical and chemical to food and others, require enantiomerically pure compounds for the development of their products. Enantiomers are non superposing specular images of a compound that has chiral properties. Many drugs contain chiral active compounds and in some cases, depending on the particular enantiomer used, the therapeutic effect may vary greatly.

This is the reason it is so important today to develop methods to produce enatiomers in a pure form; and also explains why the asymmetric synthesis procedures that produce only the desired enantiomer by means of a catalyst are now the focus of many investigations. Nevertheless, the great surge in development of this type of processes requires the parallel development of new analytical methods capable of evaluating the results obtained based on yield and enantiometric excess.

In 2001, the American chemist K.B. Sharpless was awarded the noble prize in chemistry for the development of a highly enantioselective process to obtain chiral epoxides from allyl alcohols using chiral titanium tartrate. This process is of great significance, since epoxides are widely used in organic synthesis processes as they are useful and versatile molecules that can suffer a large number of transformations due to their high reactivity. Examples can be found in ß-blockers, like Propranolol and for the synthesis of hepatitis B virus inhibitors.

The importance of these compounds and the constant research for new catalytic systems justify the need for the development of analytical methods that allow a simple, quick and efficient evaluation of these processes. For this reason, a research group at the Department of Inorganic and Analytical Chemistry at the Rey Juan Carlos University formed by the Doctors. S. Morante-Zarcero, I. del Hierro, M. Fajardo & I. Sierra, has developed and validated different analytical methods for the determination of such compounds by means of high efficiency liquid chromatography with ultraviolet detection and mass spectrometry (HPLC-DAD and HPLC-MS). Furthermore, in the last few years capillary electrophoresis (CE) has proved its great potential to carry out chiral separations. Thanks to its high efficiency, low reactive consumption and versatility, Professor. Mª Luisa Marina, in collaboration with Dr. Antonio Crego from the Department of Analytical Chemistry at the Alcalá University, applied this technique to develop the first methods using CE to determine chiral epoxides in this type of samples.

All the methodologies that were developed, and that have proven to have good characterising attributes, like linearity, precision, selectivity, detection limit, and quantification, have been used to successfully evaluate asymmetric epoxidation processes of allyl alcohols, using new chiral catalyst compounds based on titanium and have been published in analytical chemistry magazines such as the Journal of Chromatography A, Analytica Chimica Acta and Electrophoresis.

Oficina Información Científica | Source: alphagalileo
Further information: www.madrimasd.org

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